Ag(I)-Catalyzed Regioselective Ring-Opening of N-Tosylaziridine and N-Tosylazetidine with S-, O-, and N-Nucleophiles and Tethered Dinucleophiles

被引：43

作者：

Bera, Milan ^{[1
]}

Pratihar, Sanjay ^{[1
]}

Roy, Sujit ^{[1
,2
]}

机构：

[1] Indian Inst Technol, Dept Chem, Organometall & Catalysis Lab, Kharagpur 721302, W Bengal, India

[2] Indian Inst Technol, Sch Basic Sci, Bhubaneswar 751013, Orissa, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 05期

关键词：

EFFICIENT METHOD; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ACTIVATED AZIRIDINES; SELECTIVE ALKYLATION; ASYMMETRIC-SYNTHESIS; CHIRAL AZIRIDINES; FACILE SYNTHESIS; C-ARYLATION; IN-SITU;

D O I：

10.1021/jo102285z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[Ag(COD)(2)]PF6 catalyzes the ring-opening of N-tosylaziridines and -azetidines with alcohols, amines, thiols, and related tethered 1,2-ethane dinucleophiles. Initial rate studies and DFT-based evaluation of stepwise energetics suggest an inverse relationship between the nucleophilic reactivity of a heteroatom donor and its binding affinity to cationic Ag(I).

引用

页码：1475 / 1478

页数：4

共 76 条

[1] Stereochemistry of the reaction of the inhibitor β-chloroalanine with mercaptoethanol, a β-substitution reaction catalysed by an aminotransferase [J].

Adams, B ;

Beresford, KJM ;

Whyte, SM ;

Young, DW .

CHEMICAL COMMUNICATIONS, 2000, (07) :619-620

[2] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].

Ager, DJ ;

Prakash, I ;

Schaad, DR .

CHEMICAL REVIEWS, 1996, 96 (02) :835-875

[3]

Ager DJ, 1997, ALDRICHIM ACTA, V30, P3

[4] Preparation of cysteinol derivatives by highly regioselective ring opening of nonactivated chiral aziridines by thiols [J].

Bae, JH ;

Shin, SH ;

Park, CS ;

Lee, WK .

TETRAHEDRON, 1999, 55 (33) :10041-10046

[5] Unprotected Vinyl Aziridines: Facile Synthesis and Cascade Transformations [J].

Baktharaman, Sivaraj ;

Afagh, Nicholas ;

Vandersteen, Adelle ;

Yudin, Andrei K. .

ORGANIC LETTERS, 2010, 12 (02) :240-243

[6] A facile C-arylation of N-tosyl aziridines via Ag(I) catalysis [J].

Bera, Milan ;

Roy, Sujit .

TETRAHEDRON LETTERS, 2007, 48 (40) :7144-7146

[7] Silver(I)-Diene Complexes as Versatile Catalysts for the C-Arylation of N-Tosylaziridines: Mechanistic Insight from In Situ Diagnostics [J].

Bera, Milan ;

Roy, Sujit .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (13) :4402-4412

[8] Silver(I)-Catalyzed Dual Activation of Propargylic Alcohol and Aziridine/Azetidine: Triggering Ring-Opening and Endo-Selective Ring-Closing in a Cascade [J].

Bera, Milan ;

Roy, Sujit .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22) :8814-8817

[9]

Bergmeier SC, 2009, PROG HET CH, V20, P47

[10]

Bergmeier SC, 2009, PROG HET CH, V21, P69, DOI 10.1016/S0959-6380(09)70030-3

← 1 2 3 4 5 6 7 8 →